2-噻唑硼酸频那醇酯 | 214360-88-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 2-噻唑硼酸频那醇酯
• 英文名称: 2-(Thiazole-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole；2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole
• CAS: 214360-88-0
• 化学式: C₉H₁₄BNO₂S
• mdl: MFCD08061338
• 分子量: 211.093
• InChiKey: RLBBSGRLQOBNCN-UHFFFAOYSA-N

物化性质

• 沸点：
  235℃
• 密度：
  1.12
• 闪点：
  96℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-噻唑硼酸频那醇酯 、 5-iodo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 12.0h， 生成 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(thiazol-2-yl)pyridin-2-amine
  参考文献：
  名称：

  Structure Based Drug Design of Crizotinib (PF-02341066), a Potent and Selective Dual Inhibitor of Mesenchymal–Epithelial Transition Factor (c-MET) Kinase and Anaplastic Lymphoma Kinase (ALK)

  摘要：

  Because of the critical roles of aberrant signaling in cancer, both c-MET and ALK receptor tyrosine kinases are attractive oncology targets for therapeutic intervention. The cocrystal structure of 3 (PHA-665752), bound to c-MET kinase domain, revealed a novel ATP site environment, which served as the target to guide parallel, multiattribute drug design. A novel 2-amino-5-aryl-3-benzyloxypyridine series was created to more effectively make the key interactions achieved with 3. In the novel series, the 2-aminopyridine core allowed a 3-benzyloxy group to reach into the same pocket as the 2,6-dichlorophenyl group of 3 via a more direct vector and thus with a better ligand efficiency (LE). Further optimization of the lead series generated the clinical candidate crizotinib (PF-02341066), which demonstrated potent in vitro and in vivo c-MET kinase and ALK inhibition, effective tumor growth inhibition, and good pharmaceutical properties.

  DOI：

  10.1021/jm2007613

文献信息

• Fusaric acid and analogues as Gram-negative bacterial quorum sensing inhibitors
  作者：Truong Thanh Tung、Tim Holm Jakobsen、Trong Tuan Dao、Anja Thoe Fuglsang、Michael Givskov、Søren Brøgger Christensen、John Nielsen

  DOI：10.1016/j.ejmech.2016.11.044

  日期：2017.1

  microwave-assisted synthesis, efficient and expedite procedures for preparation of a library of fusaric acid and 39 analogues are reported. The fusaric acid analogues were tested in cell-based screening assays for inhibition of the las and rhl quorum sensing system in Pseudomonas aeruginosa and the lux quorum sensing system in Vibrio fischeri. Eight of the 40 compounds in the library including fusaric

  据报道，利用微波辅助合成，高效而快捷的程序可用于制备岩藻酸和39种类似物。在基于细胞的筛选试验中测试了岩藻酸类似物对铜绿假单胞菌的las和rhl群体感应系统和费氏弧菌的lux群体感应系统的抑制作用。文库中的40种化合物中有8种（包括富马酸）抑制了lux quorum感应，而一种化合物抑制了las quorum感应系统的活性。令我们高兴的是，在所测试的浓度范围内，没有一种化合物显示出生长抑制作用。
• Structure Based Drug Design of Crizotinib (PF-02341066), a Potent and Selective Dual Inhibitor of Mesenchymal–Epithelial Transition Factor (c-MET) Kinase and Anaplastic Lymphoma Kinase (ALK)
  作者：J. Jean Cui、Michelle Tran-Dubé、Hong Shen、Mitchell Nambu、Pei-Pei Kung、Mason Pairish、Lei Jia、Jerry Meng、Lee Funk、Iriny Botrous、Michele McTigue、Neil Grodsky、Kevin Ryan、Ellen Padrique、Gordon Alton、Sergei Timofeevski、Shinji Yamazaki、Qiuhua Li、Helen Zou、James Christensen、Barbara Mroczkowski、Steve Bender、Robert S. Kania、Martin P. Edwards

  DOI：10.1021/jm2007613

  日期：2011.9.22

  Because of the critical roles of aberrant signaling in cancer, both c-MET and ALK receptor tyrosine kinases are attractive oncology targets for therapeutic intervention. The cocrystal structure of 3 (PHA-665752), bound to c-MET kinase domain, revealed a novel ATP site environment, which served as the target to guide parallel, multiattribute drug design. A novel 2-amino-5-aryl-3-benzyloxypyridine series was created to more effectively make the key interactions achieved with 3. In the novel series, the 2-aminopyridine core allowed a 3-benzyloxy group to reach into the same pocket as the 2,6-dichlorophenyl group of 3 via a more direct vector and thus with a better ligand efficiency (LE). Further optimization of the lead series generated the clinical candidate crizotinib (PF-02341066), which demonstrated potent in vitro and in vivo c-MET kinase and ALK inhibition, effective tumor growth inhibition, and good pharmaceutical properties.